Hydrogen bonding in 2-carboxy-anilinium dihydrogen phosphite at 100 K.

The title compound, C(7)H(8)NO(2) (+)·H(2)PO(3) (-), is formed from alternating layers of organic cations and inorganic anions stacked along the a-axis direction. They are associated via O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonding, giving rise to two different R(2) (2)(8) graph-set motifs and generating a three-dimensional network.

Related literature

For applications of hybrid compounds, see: Kagan et al. (1999 ▶); Mazeaud et al. (2000 ▶); Benali-Cherif, Direm et al. (2007 ▶). For applications of anthranilic acid derivatives, see: He et al. (2003 ▶); Per Wiklund et al. (2004 ▶); Congiu et al. (2005 ▶); Nittoli et al. (2005 ▶). For related structured, see: Bendeif et al. (2003 ▶, 2009 ▶); Benali-Cherif, Allouche et al. (2007 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H8NO2 +·H2PO3 −

M = 219.13

Triclinic,

a = 4.8757 (6) Å

b = 9.4597 (6) Å

c = 10.0801 (5) Å

α = 78.929 (3)°

β = 76.058 (4)°

γ = 86.814 (2)°

V = 442.81 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.25 × 0.18 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Saphire2 diffractometer

Absorption correction: integration (ABSORB; DeTitta, 1985 ▶) T min = 0.972, T max = 0.985

11058 measured reflections

2581 independent reflections

2559 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 1.07

2581 reflections

127 parameters

H-atom parameters not refined

Δρmax = 0.58 e Å−3

Δρmin = −0.24 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007077/bg2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007077/bg2238Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H8NO2+·H2PO3−	Z = 2
Mr = 219.13	F(000) = 228
Triclinic, P1	Dx = 1.643 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8757 (6) Å	Cell parameters from 11058 reflections
b = 9.4597 (6) Å	θ = 2.8–32.7°
c = 10.0801 (5) Å	µ = 0.31 mm−1
α = 78.929 (3)°	T = 100 K
β = 76.058 (4)°	Prism, colourless
γ = 86.814 (2)°	0.25 × 0.18 × 0.05 mm
V = 442.81 (7) Å3

Oxford Diffraction Xcalibur Saphire2 diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	2559 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 8.4221 pixels mm-1	θmax = 30.0°, θmin = 2.8°
ω and θ scans	h = −6→6
Absorption correction: integration (ABSORB; DeTitta, 1985)	k = −12→13
Tmin = 0.972, Tmax = 0.985	l = 0→14
11058 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.093	H-atom parameters not refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2002P] where P = (Fo2 + 2Fc2)/3
2581 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	1.22190 (19)	0.11913 (10)	0.23669 (10)	0.01503 (19)
H1	1.3765	0.1163	0.1783	0.023*
O2	1.18445 (19)	0.33344 (10)	0.10200 (9)	0.01319 (18)
N1	0.6956 (2)	0.48161 (11)	0.14593 (10)	0.0107 (2)
H1A	0.5423	0.5400	0.1407	0.013*
H1B	0.7309	0.4308	0.0754	0.013*
H1C	0.8484	0.5361	0.1386	0.013*
C1	1.0902 (2)	0.24260 (13)	0.20403 (12)	0.0109 (2)
C2	0.8201 (2)	0.26393 (13)	0.30600 (12)	0.0106 (2)
C3	0.6396 (3)	0.38167 (13)	0.27952 (12)	0.0104 (2)
C4	0.3987 (3)	0.40572 (13)	0.37899 (13)	0.0131 (2)
H4	0.2794	0.4862	0.3601	0.016*
C5	0.3322 (3)	0.31144 (14)	0.50686 (13)	0.0150 (2)
H5	0.1688	0.3284	0.5755	0.018*
C6	0.5051 (3)	0.19272 (15)	0.53363 (13)	0.0157 (2)
H6	0.4584	0.1276	0.6199	0.019*
C7	0.7466 (3)	0.16969 (14)	0.43364 (13)	0.0141 (2)
H7	0.8639	0.0883	0.4525	0.017*
P1	0.19035 (6)	0.80587 (3)	0.08601 (3)	0.01016 (10)
O3	0.29056 (19)	0.88933 (10)	−0.06075 (9)	0.01379 (18)
O4	0.20062 (18)	0.64347 (9)	0.10464 (9)	0.01255 (18)
O5	−0.1212 (2)	0.85119 (10)	0.14917 (10)	0.0166 (2)
H5O	−0.1511	0.9363	0.1122	0.025*
H	0.3396	0.8447	0.1629	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0120 (4)	0.0112 (4)	0.0180 (4)	0.0041 (3)	−0.0003 (3)	0.0013 (3)
O2	0.0124 (4)	0.0120 (4)	0.0132 (4)	0.0011 (3)	−0.0016 (3)	0.0003 (3)
N1	0.0102 (5)	0.0093 (4)	0.0118 (5)	0.0016 (3)	−0.0022 (3)	−0.0011 (3)
C1	0.0102 (5)	0.0099 (5)	0.0131 (5)	0.0011 (4)	−0.0039 (4)	−0.0025 (4)
C2	0.0097 (5)	0.0101 (5)	0.0118 (5)	0.0003 (4)	−0.0030 (4)	−0.0013 (4)
C3	0.0117 (5)	0.0093 (5)	0.0101 (5)	−0.0004 (4)	−0.0031 (4)	−0.0013 (4)
C4	0.0122 (5)	0.0128 (5)	0.0141 (5)	0.0013 (4)	−0.0020 (4)	−0.0036 (4)
C5	0.0134 (5)	0.0180 (6)	0.0128 (5)	−0.0004 (4)	−0.0006 (4)	−0.0042 (4)
C6	0.0172 (6)	0.0175 (6)	0.0103 (5)	−0.0013 (5)	−0.0016 (4)	0.0014 (4)
C7	0.0137 (5)	0.0130 (6)	0.0142 (5)	0.0016 (4)	−0.0036 (4)	0.0008 (4)
P1	0.01028 (15)	0.00778 (15)	0.01211 (15)	0.00126 (10)	−0.00279 (11)	−0.00126 (10)
O3	0.0124 (4)	0.0106 (4)	0.0148 (4)	0.0029 (3)	0.0006 (3)	0.0007 (3)
O4	0.0124 (4)	0.0082 (4)	0.0166 (4)	0.0013 (3)	−0.0040 (3)	−0.0009 (3)
O5	0.0149 (4)	0.0110 (4)	0.0181 (4)	0.0053 (3)	0.0026 (3)	0.0018 (3)

O1—C1	1.3250 (14)	C4—H4	0.9500
O1—H1	0.8399	C5—C6	1.3902 (18)
O2—C1	1.2182 (15)	C5—H5	0.9500
N1—C3	1.4643 (15)	C6—C7	1.3908 (17)
N1—H1A	0.9100	C6—H6	0.9500
N1—H1B	0.9100	C7—H7	0.9500
N1—H1C	0.9101	P1—O4	1.5110 (9)
C1—C2	1.4930 (16)	P1—O3	1.5154 (9)
C2—C7	1.3970 (16)	P1—O5	1.5695 (9)
C2—C3	1.4060 (16)	P1—H	1.2947
C3—C4	1.3880 (16)	O5—H5O	0.8400
C4—C5	1.3969 (17)
C1—O1—H1	109.5	C5—C4—H4	120.1
C3—N1—H1A	109.5	C6—C5—C4	120.00 (11)
C3—N1—H1B	109.5	C6—C5—H5	120.0
H1A—N1—H1B	109.5	C4—C5—H5	120.0
C3—N1—H1C	109.5	C5—C6—C7	119.76 (12)
H1A—N1—H1C	109.5	C5—C6—H6	120.1
H1B—N1—H1C	109.5	C7—C6—H6	120.1
O2—C1—O1	123.21 (11)	C6—C7—C2	121.25 (12)
O2—C1—C2	122.48 (11)	C6—C7—H7	119.4
O1—C1—C2	114.27 (10)	C2—C7—H7	119.4
C7—C2—C3	118.21 (11)	O4—P1—O3	116.92 (5)
C7—C2—C1	120.31 (11)	O4—P1—O5	107.62 (5)
C3—C2—C1	121.42 (11)	O3—P1—O5	109.90 (5)
C4—C3—C2	120.87 (11)	O4—P1—H	108.37
C4—C3—N1	117.68 (10)	O3—P1—H	108.24
C2—C3—N1	121.44 (10)	O5—P1—H	105.16
C3—C4—C5	119.89 (11)	P1—O5—H5O	109.5
C3—C4—H4	120.1
O2—C1—C2—C7	−168.18 (12)	C2—C3—C4—C5	−0.57 (19)
O1—C1—C2—C7	9.66 (16)	N1—C3—C4—C5	178.45 (11)
O2—C1—C2—C3	9.07 (18)	C3—C4—C5—C6	−0.83 (19)
O1—C1—C2—C3	−173.09 (11)	C4—C5—C6—C7	1.1 (2)
C7—C2—C3—C4	1.67 (18)	C5—C6—C7—C2	0.1 (2)
C1—C2—C3—C4	−175.63 (11)	C3—C2—C7—C6	−1.42 (18)
C7—C2—C3—N1	−177.31 (11)	C1—C2—C7—C6	175.92 (12)
C1—C2—C3—N1	5.39 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.84	1.77	2.6085 (13)	178
N1—H1A···O4	0.91	1.96	2.8589 (14)	169
N1—H1B···O4ii	0.91	2.02	2.9160 (13)	169
N1—H1C···O4iii	0.91	1.97	2.8740 (14)	173
O5—H5O···O3iv	0.84	1.78	2.6059 (13)	167
C6—H6···O5v	0.95	2.55	3.2542 (15)	132
C7—H7···O1	0.95	2.42	2.7503 (16)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.84	1.77	2.6085 (13)	178
N1—H1A⋯O4	0.91	1.96	2.8589 (14)	169
N1—H1B⋯O4ii	0.91	2.02	2.9160 (13)	169
N1—H1C⋯O4iii	0.91	1.97	2.8740 (14)	173
O5—H5O⋯O3iv	0.84	1.78	2.6059 (13)	167
C6—H6⋯O5v	0.95	2.55	3.2542 (15)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .